Hydrochloric Acid → HCID 22260960, compound

HRID 1610128Notes

Reaction equation

C([Li])CCC.C(NC(C)C)(C)C.[Br:13][C:14]1[CH:15]=[CH:16][C:17]([F:21])=[C:18]([CH3:20])[CH:19]=1.[F:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH:26]=[O:27].Cl>CCCCCC.O1CCCC1.C(OCC)(=O)C>[Br:13][C:14]1[CH:19]=[C:18]([CH3:20])[C:17]([F:21])=[C:16]([CH:26]([C:25]2[CH:28]=[CH:29][CH:30]=[C:23]([F:22])[CH:24]=2)[OH:27])[CH:15]=1

Participants

Conditions

Temperature: -78 °C

Procedure

In an atmosphere of nitrogen gas, 74.1 ml of a 1.57 M solution of n-butyllithium in hexane was added to a solution of 16.3 ml of N,N-diisopropylamine in 400 ml tetrahydrofuran at 0° C., and the mixture was stirred at the same temperature for 30 minutes. After cooling to −78° C., a solution of 20.0 g of 5-bromo-2-fluorotoluene in 40 ml tetrahydrofuran was added dropwise. After stirring at the same temperature for 1 hour, 11.2 ml of 3-fluorobenzaldehyde was added dropwise and the mixture was stirred at the same temperature for 3 hours. The reaction mixture was neutralized with 1 N hydrochloric acid and diluted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated. The crude product was purified and separated by silica gel column chromatography (ethyl acetate:n-hexane=1:20), to give 20.6 g of the title compound as a colorless oil.

Workup

stirringAfter stirring at the same temperature for 1 hour
stirringthe mixture was stirred at the same temperature for 3 hours
washThe organic layer was washed with brine
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was evaporated
customThe crude product was purified
customseparated by silica gel column chromatography (ethyl acetate:n-hexane=1:20)

Sources & evidence

ORD record: ord-40b79e550cd94207bf3078969146f81e
Source dataset: uspto-grants-2006_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06982274B2

Reaction notes

Loading…